Photosensitive resin composition, cured film, and semiconductor device

Abstract

A photosensitive resin composition of the present invention comprises: a polymer A having a constituent unit represented by general formula (a) below; and a polymer B containing a polyimide having a group b represented by general formula (b) below.

Description

Technical Field

[0001] The present invention relates to a photosensitive resin composition, a cured film, and a semiconductor device.

Background Art

[0002] Polyimide resins are widely used as thin films for electronic materials such as protective materials, insulating materials, and color filters in liquid crystal display elements and semiconductors because they have high mechanical strength, heat resistance, insulation properties, and solvent resistance.

[0003] Patent Document 1 discloses a photosensitive composition containing a polyimide having a predetermined maleimide group at its terminal. Patent Document 2 discloses an optical waveguide having a core portion containing a first compound having a functional group capable of dimerizing by light irradiation. As the first compound, a cyclic olefin resin having a predetermined maleimide group at its terminal as the functional group capable of dimerizing is exemplified.

Prior Art Documents

Patent Documents

[0004]

Patent Document 1

Patent Document 2

Summary of the Invention

Problems to be Solved by the Invention

[0005] However, in the conventional technologies described in Patent Documents 1 and 2, there is room for improvement in the dielectric tangent and mechanical strength of cured films obtained from the photosensitive resin composition.

Means for Solving the Problems

[0006] The inventors of the present invention have found that the above problems can be solved by using a combination of a polyimide having a specific structure and a cyclic olefin resin, and have completed the present invention. That is, the present invention can be shown as follows.

[0007] According to the present invention, a polymer A having a structural unit represented by the following general formula (a), a polymer B containing a polyimide having a group b represented by the following general formula (b), and a photosensitive resin composition containing the same can be provided.

Chemical formula

Chemical formula

[0008] According to the present invention, a cured film composed of a cured product of the photosensitive resin composition can be provided.

[0009] According to the present invention, a semiconductor device including a resin film containing a cured product of the photosensitive resin composition can be provided.

Effects of the Invention

[0010] The photosensitive resin composition of the present invention can yield cured products such as films that exhibit excellent low dielectric loss tangent and superior mechanical properties. [Brief explanation of the drawing]

[0011] [Figure 1] This is a schematic cross-sectional view of the semiconductor device according to this embodiment. [Modes for carrying out the invention]

[0012] Embodiments of the present invention will be described below with reference to the drawings. In all drawings, similar components are denoted by the same reference numerals, and their descriptions are omitted as appropriate. Also, for example, "1 to 10" represents "1 or more" to "10 or less" unless otherwise specified.

[0013] The photosensitive resin composition of this embodiment comprises polymer A and polymer B. As a result, the photosensitive resin composition of this embodiment can produce cured products such as films that have excellent low dielectric loss tangent and excellent mechanical properties. The following explains each component.

[0014] [Polymer A] Polymer A has a constituent unit (a) represented by the following general formula (a).

[0015] [ka]

[0016] In general formula (a), R 1 and R 2 Each of these independently represents a hydrogen atom or an alkyl group having 1 to 3 carbon atoms, R 1 and R 2At least one of them is preferably an alkyl group having 1 to 3 carbon atoms, and more preferably both are alkyl groups having 1 to 3 carbon atoms. From the viewpoint of the effects of the present invention, alkyl groups having 1 or 2 carbon atoms are preferred as the alkyl groups having 1 to 3 carbon atoms, and alkyl groups having 1 carbon atom are more preferred.

[0017] Q 1 This indicates a single bond or a divalent organic group. As the divalent organic group, any organic group known within the range that achieves the effects of the present invention can be used, but examples include an alkylene group having 1 to 8 carbon atoms or a (poly)alkylene glycol chain. The alkylene group having 1 to 8 carbon atoms is preferably an alkylene group having 2 to 6 carbon atoms.

[0018] Examples of alkylene groups having 1 to 8 carbon atoms include methylene, ethylene, propylene, butylene, pentylene, hexylene, heptylene, and octylene groups.

[0019] The alkylene oxides constituting the (poly)alkylene glycol chain are not particularly limited, but are preferably composed of alkylene oxides having 1 to 18 carbon atoms, and more preferably alkylene oxides having 2 to 8 carbon atoms. Examples include ethylene oxide, propylene oxide, butylene oxide, isobutylene oxide, 1-butene oxide, 2-butene oxide, trimethylethylene oxide, tetramethylene oxide, tetramethylethylene oxide, butadiene monooxide, octylene oxide, and the like.

[0020] G 1 , G 2 , and G 3 Each of these independently represents a hydrogen atom, a substituted or unsubstituted hydrocarbon group having 1 to 30 carbon atoms, or a hydrogen atom.

[0021] Examples of hydrocarbon groups having 1 to 30 carbon atoms include alkyl groups, alkenyl groups, alkynyl groups, alkylidene groups, aryl groups, aralkyl groups, alkalil groups, or cycloalkyl groups.

[0022] Examples of alkyl groups include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, pentyl, neopentyl, hexyl, heptyl, octyl, nonyl, and decyl groups. Examples of alkenyl groups include allyl, pentenyl, and vinyl groups. An example of an alkynyl group is the ethynyl group. Examples of alkylidene groups include the methylidene group and the ethylidene group.

[0023] Examples of aryl groups include phenyl, naphthyl, and anthracenyl groups. Examples of aralkyl groups include benzyl and phenethyl groups.

[0024] Examples of alkaryl groups include tolyl and xylyl groups. Examples of cycloalkyl groups include adamantyl, cyclopentyl, cyclohexyl, and cyclooctyl groups. A hydrocarbon group having 1 to 30 carbon atoms may contain at least one atom selected from O, N, S, P, and Si in its structure.

[0025] In this embodiment, the hydrocarbon group having 1 to 30 carbon atoms is preferably a hydrocarbon group having 1 to 15 carbon atoms, and more preferably a hydrocarbon group having 1 to 10 carbon atoms. Furthermore, the hydrocarbon group having 1 to 30 carbon atoms is preferably an alkyl group having 1 to 30 carbon atoms, more preferably an alkyl group having 1 to 15 carbon atoms, and even more preferably an alkyl group having 1 to 10 carbon atoms.

[0026] Substituents of C1-C30 hydrocarbon groups can include hydroxyl groups, amino groups, cyano groups, ester groups, ether groups, amide groups, sulfonamide groups, etc., and may be substituted with at least one of these groups.

[0027] In this embodiment, G 1 , G 2 , and G 3 Preferably, one of them is a substituted or unsubstituted hydrocarbon group having 1 to 30 carbon atoms, and the rest are hydrogen atoms; more preferably, all are hydrogen atoms. m is 0, 1, or 2, preferably 0 or 1, and more preferably 0.

[0028] Polymer A in this embodiment has a structure represented by general formula (a), and therefore exhibits excellent low dielectric loss tangent. Furthermore, polymer A has a predetermined maleimide group in its side chain, and since radical reactions do not occur and photodimerization is possible, polymer A can be photopolymerized with other polymers, and polymer A can be photopolymerized with the polyimide contained in polymer B described later, resulting in superior mechanical strength.

[0029] Polymer A of this embodiment can be synthesized as follows. First, the compound (a') represented by the following general formula (a') is subjected to addition polymerization, and if necessary, further addition polymerization is carried out with other norbornene-based compounds to obtain a polymer. For example, addition polymerization is carried out by coordination polymerization. [ka]

[0030] In general formula (a'), R 1 , R 2 Q 1 , G 1 , G 2 , G 3 And m is synonymous with general formula (a).

[0031] Other norbornene compounds include norbornenes having alkyl groups such as 5-methylnorbornene, 5-ethylnorbornene, 5-butylnorbornene, 5-hexylnorbornene, 5-decylnorbornene, 5-cyclohexylnorbornene, and 5-cyclopentylnorbornene; norbornenes having alkenyl groups such as 5-ethylidenenorbornene, 5-vinylnorbornene, 5-propenylnorbornene, 5-cyclohexenylnorbornene, and 5-cyclopentenylnorbornene; and norbornenes having aromatic rings such as 5-phenylnorbornene, 5-phenylmethylnorbornene, 5-phenylethylnorbornene, and 5-phenylpropylnorbornene.

[0032] In this embodiment, solution polymerization can be carried out by dissolving the above compound and an organometallic catalyst in a solvent and then heating for a predetermined time. At this time, the heating temperature can be, for example, 30°C to 200°C, preferably 40°C to 150°C, and more preferably 50°C to 120°C. In this embodiment, the yield of polymer (A) can be improved by using a higher heating temperature than in the conventional method.

[0033] Furthermore, the heating time can be, for example, 0.5 hours to 72 hours. It is more preferable to remove dissolved oxygen from the solvent by nitrogen bubbling before performing solution polymerization.

[0034] Furthermore, molecular weight modifiers and chain transfer agents can be used as needed. Examples of chain transfer agents include alkylsilane compounds such as trimethylsilane, triethylsilane, and tributylsilane. These chain transfer agents may be used individually or in combination of two or more.

[0035] As solvents used in the above polymerization reaction, for example, one or more of the following can be used: methyl ethyl ketone (MEK), propylene glycol monomethyl ether, diethyl ether, tetrahydrofuran (THF), toluene, ethyl acetate, butyl acetate and other esters, and alcohols such as methyl alcohol, ethyl alcohol, and isopropyl alcohol.

[0036] The organometallic catalysts mentioned above are not particularly selected as long as addition polymerization proceeds. For example, ligands such as phosphine-based or diimine-based ligands may be coordinated to the palladium complex and nickel complex, and counteranions may also be used. One or more of these can be used.

[0037] Examples of the above palladium complexes include (acetato-κ0)(acetonitrile)bis[tris(1-methylethyl)phosphine]palladium(I)tetrakis(2,3,4,5,6-pentafluorophenyl)borate, π-allylpalladium chloride dimer, and other allylpalladium complexes. Palladium organic carboxylates such as palladium acetate, propionate, maleate, and naphthoate, Palladium organic carboxylic acid complexes such as palladium acetate triphenylphosphine complex, palladium acetate tri(m-tolyl)phosphine complex, and palladium acetate tricyclohexylphosphine complex. Palladium dibutyl phosphate, p-toluenesulfonate and other palladium organosulfonates, Palladium β-diketone compounds such as bis(acetylacetonate)palladium, bis(hexafluoroacetylacetonate)palladium, bis(ethylacetoacetate)palladium, and bis(phenylacetoacetate)palladium. Examples include palladium halide complexes such as dichlorobis(triphenylphosphine)palladium, bis[tri(m-tolylphosphine)]palladium, dibromobis[tri(m-tolylphosphine)]palladium, and acetonyltriphenylphosphine complexes.

[0038] Examples of the phosphine ligands mentioned above include triphenylphosphine, dicyclohexylphenylphosphine, cyclohexyldiphenylphosphine, and tricyclohexylphosphine.

[0039] Examples of the above counteranions include triphenylcarbenium tetrakis(pentafluorophenyl) borate, triphenylcarbenium tetrakis[3,5-bis(trifluoromethyl)phenyl] borate, triphenylcarbenium tetrakis(2,4,6-trifluorophenyl) borate, triphenylcarbenium tetraphenyl borate, tributylammonium tetrakis(pentafluorophenyl) borate, N,N-dimethylanilinium tetrakis(pentafluorophenyl) borate, N,N-diethylanilinium tetrakis(pentafluorophenyl) borate, N,N-diphenylanilinium tetrakis(pentafluorophenyl) borate, and lithium tetrakis(pentafluorophenyl) borate.

[0040] The amount of organometallic catalyst can be 300 ppm to 5000 ppm, preferably 1000 ppm to 3500 ppm, and more preferably 1500 ppm to 2500 ppm, relative to the norbornene monomer. This can improve the yield of polymer A.

[0041] The reaction solution containing the obtained polymer A is added to, for example, an alcohol such as hexane or methanol to precipitate polymer A. Then, polymer A is filtered off, washed with, for example, an alcohol such as hexane or methanol, and then dried. In this embodiment, polymer A can be synthesized, for example, in this manner. According to the manufacturing method of this embodiment, polymer A can be obtained in a high yield of 70% or more.

[0042] The conversion rate with dialkyl maleic anhydride is preferably 30% or more. More preferably 40%, and even more preferably 50% or more. Within this range, the polyimide components that leach out during development can be reduced.

[0043] Polymer A in this embodiment may contain other constituent units other than constituent unit (a) to the extent that it achieves the effects of the present invention, and other constituent units include constituent units derived from the other norbornene compounds mentioned above.

[0044] If polymer B, described later, does not contain halogen atoms in its structure, specifically, R of general formula (b1) 5 and R 6 When is a hydrogen atom, a C1-C3 alkyl group, or a hydroxyl group, and X is a single bond, a C1-C4 alkylene group, a divalent ether group derived from bisphenol A, a divalent ether group derived from bisphenol F, or a divalent ether group derived from bisphenol S, the weight-average molecular weight of polymer A can be 3,000 to 30,000, preferably 4,000 to 20,000, and more preferably 4,500 to 15,000, from the viewpoint of compatibility between polymer A and polymer B. On the other hand, if polymer B, described later, contains halogen atoms in its structure, specifically R of general formula (b1) 5 , R 6 If either X is a halogen atom-containing group, polymer B exhibits excellent compatibility. Therefore, from the viewpoint of compatibility between polymer A and polymer B, the weight-average molecular weight of polymer A can be 3,000 to 300,000, preferably 4,000 to 250,000, and more preferably 4,500 to 200,000.

[0045] [Polymer B] Polymer B contains a polyimide having a group b represented by the following general formula (b).

[0046] [ka]

[0047] In general formula (b), R 3 and R 4 Each of these independently represents a hydrogen atom or an alkyl group having 1 to 3 carbon atoms, R 3 and R 4 At least one of them is preferably a C1-C3 alkyl group, and more preferably both are C1-C3 alkyl groups. From the viewpoint of the effects of the present invention, a C1 or C2 alkyl group is preferred as the C1-C3 alkyl group, and a C1 alkyl group is more preferred. * indicates a bond.

[0048] G 4 Each of these independently represents a hydrogen atom, a substituted or unsubstituted hydrocarbon group with 1 to 30 carbon atoms, and a substituted or unsubstituted hydrocarbon group with 1 to 30 carbon atoms. 1 , G 2 , and G 3 It is synonymous with the one in [the relevant context]. In this embodiment, there are multiple G 4 Preferably, one of them is a substituted or unsubstituted hydrocarbon group having 1 to 30 carbon atoms, and the rest are hydrogen atoms; more preferably, all are hydrogen atoms.

[0049] Q 2 This indicates a divalent organic group. As the divalent organic group, any organic group known within the range that achieves the effects of the present invention can be used, but for example, an organic group represented by the following general formula (b1) can be cited.

[0050] [ka]

[0051] In general formula (b1), R 5 and R 6Each of these independently represents a hydrogen atom, a C1-C4 haloalkyl group, a C1-C3 alkyl group, a C1-C3 alkoxy group, or a hydroxyl group, with a C1-C3 alkyl group or a C1-C4 haloalkyl group being preferred, and a C1-C2 alkyl group or a C1-C2 haloalkyl group being more preferred.

[0052] The C1-C4 haloalkyl group may be linear or branched, and may include fluoromethyl, difluoromethyl, trifluoromethyl, 2-fluoroethyl, 1,1,2-trifluoroethyl, 1,1,2,2-tetrafluoroethyl, 2,2,2-trifluoroethyl, pentafluoroethyl, 3-fluoropropyl, heptafluoropropyl, 1,1,2,3,3,3-hexafluoropropyl, and 1,2,2,3,3,3-hexafluoropropyl. Examples include the chloromethyl group, 4-fluorobutyl group, nonafluorobutyl group; chloromethyl group, dichloromethyl group, trichloromethyl group, 2-chloroethyl group, 1,1,2-trichloroethyl group, 1,1,2,2-tetrachloroethyl group, 2,2,2-trichloroethyl group, pentachloroethyl group, 3-chloropropyl group, heptachloropropyl group, hexachloropropyl group, 1,2,2,3,3,3-hexachloropropyl group, 4-chlorobutyl group, nonachlorobutyl group, etc. Examples of alkyl groups having 1 to 3 carbon atoms include methyl, ethyl, n-propyl, and isopropyl groups. Examples of alkoxy groups having 1 to 3 carbon atoms include methoxy, ethoxy, n-propoxy, and isopropoxy groups.

[0053] X represents a single bond, a C1-C4 alkylene group, a C1-C4 haloalkylene group, a divalent ether group derived from bisphenol A, a divalent ether group derived from bisphenol F, a divalent ether group derived from bisphenol S, or a divalent ether group derived from hexafluorobisphenol A. A single bond or a C1-C4 alkylene group is preferred, and a single bond or a C1-C2 alkylene group is more preferred. Examples of alkylene groups having 1 to 4 carbon atoms include methylene, ethylene, trimethylene, propylene, and butylene groups.

[0054] Examples of haloalkylene groups having 1 to 4 carbon atoms include fluoromethylene, difluoromethylene, fluoroethylene, 1,2-difluoroethylene, trifluoroethylene, perfluoroethylene, perfluoropropylene, perfluorobutylene, chloromethylene, chloroethylene, chloropropylene, bromomethylene, bromoethylene, bromopropylene, methylene iodide, ethylene iodide, and propylene iodide. * indicates a bond.

[0055] From the viewpoint of the effects of the present invention, it is preferable that polymer B contains a polyimide having at least one end, preferably both ends, of a group b represented by the general formula (b).

[0056] Polymer B in this embodiment has excellent mechanical strength because it possesses a group b represented by general formula (b). Furthermore, since the polyimide has a predetermined maleimide group at its terminal, and photodimerization is possible without radical reactions, the polyimides contained in polymer B can be photopolymerized with each other, and polymer A can be photopolymerized with the polyimide, resulting in even greater mechanical strength.

[0057] Furthermore, polymer (B) may include a polyimide having at least one end a group c represented by the following general formula (c).

[0058] [ka]

[0059] In general formula (c), R 5 , R 6 X is synonymous with general formula (b1), G 4 This is equivalent to general formula (b).

[0060] If the polyimide contained in polymer (B) includes a polyimide comprising the group c, the ratio of the number of moles of group b to the total number of moles of group b and group c (b / b+c) can be 0.50 or more, preferably 0.55 or more, and more preferably 0.60 or more. Within this range, the polyimide components that leach during development can be reduced.

[0061] From the viewpoint of the effects of the present invention, polymer B preferably contains a polyimide represented by the following general formula (d).

[0062] [ka]

[0063] In general formula (d), R 3 , R 4 Q 2 This is equivalent to the general formula (b) above, and there are multiple R 3 Multiple Rs exist. 4 Multiple Qs exist. 2 Multiple G 4 The individuals may be the same or different.

[0064] Y is selected from the groups represented by the following general formulas (d1), (d2), and (d3), and from the haloalkylene groups having 1 to 5 carbon atoms. Multiple Ys may be the same or different.

[0065] [ka]

[0066] In general formula (d1), R 7 and R 8 Each of these independently represents a hydrogen atom, a C1-C3 alkyl group, and a C1-C3 alkoxy group, and there are multiple R groups. 7 Multiple Rs exist. 8 The elements can be identical or different. * indicates a bonding action.

[0067] R7 and R 8 From the viewpoint of the effects of the present invention, it is preferably a hydrogen atom or an alkyl group having 1 to 3 carbon atoms, and more preferably R 7 at least one of and R 8 At least one of them is an alkyl group having 1 to 3 carbon atoms, and more preferably three R 7 is an alkyl group having 1 to 3 carbon atoms and one R 7 It is a hydrogen atom and has three R 8 is an alkyl group having 1 to 3 carbon atoms and one R 8 is a hydrogen atom, and particularly preferably three R 7 It is a methyl group and one R 7 It is a hydrogen atom and has three R 8 It is a methyl group and one R 8 That is a hydrogen atom. * indicates a bond.

[0068] In general formula (d2), R 9 and R 10 Each of these independently represents a hydrogen atom, a C1-C3 alkyl group, and a C1-C3 alkoxy group, and there are multiple R groups. 9 Multiple Rs exist. 10 They may be the same or different.

[0069] R 9 and R 10 From the viewpoint of the effects of the present invention, it is preferably a hydrogen atom or an alkyl group having 1 to 3 carbon atoms, and more preferably a hydrogen atom.

[0070] R 11 R represents a hydrogen atom, an alkyl group having 1 to 3 carbon atoms, or an alkoxy group having 1 to 3 carbon atoms, and there are multiple R groups. 11 They may be the same or different. R 11 From the viewpoint of the effects of the present invention, it is preferably a hydrogen atom or an alkyl group having 1 to 3 carbon atoms, and more preferably a hydrogen atom. * indicates a bond.

[0071] In the general formula (d3), Z represents an alkylene group having 1 to 5 carbon atoms, or a divalent aromatic group. Examples of divalent aromatic groups include phenylene groups, divalent biphenyl groups, and naphthylene groups. * indicates a bond.

[0072] In this embodiment, the polyimide contains a compound (polymer) in which Y has groups represented by the general formulas (d1), (d2), and (d3) in its main chain. As a result, the polymer main chain can withstand deformation, and the sliding between polymer chains is improved, leading to a significant improvement in elongation, excellent mechanical strength, and suppressed curing shrinkage, resulting in a cured product such as a film with excellent dimensional stability.

[0073] In the above general formula (d), Q 3 This represents a repeating unit expressed by the following general formula (d4).

[0074] [ka]

[0075] In general formula (d4), R 5 , R 6 And X is synonymous with the above general formula (b1), Y is synonymous with the above general formula (d), G 4 This is equivalent to the general formula (b) above. n represents an integer between 20 and 200, preferably between 30 and 180. * indicates a bond.

[0076] The weight-average molecular weight of the polyimide contained in polymer B of this embodiment is 10,000 to 300,000, preferably 15,000 to 200,000.

[0077] Furthermore, since the polyimide of this embodiment has excellent solubility in solvents and does not need to be used as a varnish in its precursor state, a varnish containing polymer B can be prepared, and a cured product such as a film with excellent dimensional stability can be obtained from this varnish.

[0078] <Method for producing polyimide> The polyimide of this embodiment can be synthesized as follows. A diamine (i) represented by the following general formula (i) is reacted with an acid anhydride (ii) represented by the following general formula (ii) and a maleic anhydride derivative (iii) represented by the following general formula (iii).

[0079] [ka]

[0080] In general formula (i), X, R 5 , R 6 This is equivalent to general formula (b1). Diamine(i) can be one or more compounds represented by general formula (i).

[0081] [ka]

[0082] In general formula (ii), G 4 is synonymous with general formula (b), and Y is synonymous with general formula (d). Acid anhydride (ii) may be one or more compounds represented by general formula (ii).

[0083] [ka]

[0084] In general formula (iii), R 3 , R 4 This is equivalent to the general formula (b) above. The maleic anhydride derivative (iii) can be one or more compounds represented by general formula (iii).

[0085] The equivalent ratio of diamine(i) to acid anhydride(ii) in this reaction is an important factor in determining the molecular weight of the resulting polyimide. Generally, it is well known that there is a correlation between the molecular weight of a polymer and its mechanical properties, with higher molecular weights resulting in superior mechanical properties. Therefore, to obtain a polyimide with practically excellent strength, a certain degree of high molecular weight is necessary. In this invention, there are no particular restrictions on the equivalent ratio of diamine(i) to acid anhydride(ii) used, but it is preferable that the equivalent ratio of acid anhydride(ii) to diamine(i) is in the range of 0.80 to 1.06. Below 0.80, the molecular weight is low and brittle, resulting in weak mechanical strength. Above 1.06, unreacted carboxylic acid may decarboxylate during heating, generating gas and causing foaming, which is undesirable.

[0086] The amount of maleic anhydride derivative (iii) is preferably 30 mol% to 100 mol% of polynorbornene, more preferably 40 mol% to 100 mol%, and even more preferably 50 mol% to 100 mol%. This allows for the imparting of photosensitivity to polyimide through photodimerization, resulting in cured products such as films that are superior in terms of low dielectric loss tangent and mechanical properties.

[0087] This reaction can be carried out in an organic solvent by known methods. Examples of organic solvents include aprotic polar solvents such as γ-butyllactone (GBL), N,N-dimethylformamide, N,N-dimethylacetamide, tetrahydrofuran, diethylene glycol dimethyl ether, diethylene glycol diethyl ether, cyclohexanone, and 1,4-dioxane, and one or more of these may be used in combination. In this case, a nonpolar solvent that is compatible with the above aprotic polar solvent may be mixed and used. Examples of nonpolar solvents include aromatic hydrocarbons such as toluene, ethylbenzene, xylene, mesitylene, and solvent naphtha. The proportion of the nonpolar solvent in the mixed solvent can be arbitrarily set according to the stirring capacity and resin properties such as solution viscosity, as long as the solubility of the solvent does not decrease and the polyamic acid resin obtained by the reaction does not precipitate.

[0088] The reaction temperature is 0°C to 100°C, preferably 20°C to 80°C, for about 30 minutes to 2 hours, followed by a reaction at 100°C to 250°C, preferably 120°C to 200°C, for about 1 to 5 hours.

[0089] The maleic anhydride derivative (iii) may be present in the imidation reaction between the diamine (i) and the acid anhydride (ii), but the maleic anhydride derivative (iii), dissolved in the above organic solvent, can be added and reacted during or after the reaction between the diamine (i) and the acid anhydride (ii) to encapsulate the polyimide ends. When maleic anhydride derivative (iii) is added separately, it is preferable to react the mixture at a temperature of 100°C to 250°C, preferably 120°C to 200°C, for about 1 to 5 hours after addition.

[0090] By following the above steps, a reaction solution containing the polyimide (end-capped polyimide) of this embodiment can be obtained. This solution can then be further diluted with an organic solvent or the like as needed and used as a polymer solution (coating varnish). The organic solvent used can be one of those exemplified in the reaction process, and may be the same organic solvent as in the reaction process, or a different organic solvent. Alternatively, this reaction solution can be added to a poor solvent to reprecipitate the polyimide, remove unreacted monomers, and then dried and solidified. This can then be dissolved again in an organic solvent and used as a purified product. In applications where impurities and foreign substances are particularly problematic, it is preferable to dissolve it again in an organic solvent and filter it to obtain a purified varnish.

[0091] The polyimide concentration (100% by weight) in the polymer solution is not particularly limited, but is approximately 10-30% by weight.

[0092] In this embodiment, from the viewpoint of the effects of the present invention, the ratio of polymer A to polymer B (A:B) can be 5:95 to 95:5, preferably 10:90 to 90:10, more preferably 20:80 to 80:20, even more preferably 30:70 to 70:30, and particularly preferably 40:60 to 60:40.

[0093] From the viewpoint of tensile strength and elongation, the molecular weight of polymer B can be 30,000 to 200,000, preferably 40,000 to 180,000, and more preferably 50,000 to 150,000.

[0094] [Photosensitizer] The photosensitive resin composition of this embodiment may further contain a photosensitizer. Examples of photosensitizers include benzophenone-based photopolymerization initiators, thioxanthone-based photopolymerization initiators, benzyl-based photopolymerization initiators, and Michler-ketone-based photopolymerization initiators. Among these, benzophenone-based photopolymerization initiators or thioxanthone-based photopolymerization initiators are preferred.

[0095] Examples of benzophenone-based photopolymerization initiators include benzophenone, 4-chlorobenzophenone, 4,4'-dimethoxybenzophenone, 4,4'-diaminobenzophenone, 4-phenylbenzophenone, isophthalphenone, and 4-benzoyl-4'-methyl-diphenyl sulfide. These benzophenones and their derivatives can improve the curing rate by using tertiary amines as hydrogen donors.

[0096] Examples of commercially available benzophenone-based photopolymerization initiators include SPEEDCUREMBP (4-methylbenzophenone), SPEEDCUREMBB (methyl-2-benzoylbenzoate), SPPEDCUREBMS (4-benzoyl-4'methyldiphenyl sulfide), SPPEDCUREPBZ (4-phenylbenzophenone), and SPPEDCUREEMK (4,4'-bis(diethylamino)benzophenone) (all trade names, manufactured by DKSH Japan Co., Ltd.).

[0097] Examples of thioxanthone-based photopolymerization initiators include thioxanthone, diethylthioxanthone, isopropylthioxanthone, and chlorothioxanthone. 2,4-diethylthioxanthone is preferred as diethylthioxanthone, 2-isopropylthioxanthone as isopropylthioxanthone, and 2-chlorothioxanthone as chlorothioxanthone. Among these, thioxanthone-based photopolymerization initiators containing diethylthioxanthone are even more preferred.

[0098] Examples of commercially available thioxanthone-based photopolymerization initiators include SpeedcureDETX (2,4-diethylthioxanthone), SpeedcureITX (2-isopropylthioxanthone), SpeedcureCTX (2-chlorothioxanthone), SPEEDCURECPTX (1-chloro-4-propylthioxanthone) (all trade names, manufactured by DKSH Japan Co., Ltd.), and KAYACUREDETX (2,4-diethylthioxanthone) (trade name, manufactured by Nippon Kayaku Co., Ltd.).

[0099] The amount of photosensitizer added is not particularly limited, but is preferably about 0.05 to 10% by mass of the total solid content of the photosensitive resin composition, more preferably about 0.1 to 7.5% by mass, and even more preferably about 0.2 to 5% by mass. By setting the amount of photosensitizer added within the above range, the patternability of the photosensitive resin layer containing the photosensitive resin composition can be improved, and the long-term storage properties of the photosensitive resin composition can be improved.

[0100] [Adhesion enhancer] The photosensitive resin composition of this embodiment may further contain an adhesion enhancer. This improves the adhesion between the resin film or pattern formed from the photosensitive resin composition and the substrate.

[0101] The adhesion aids that can be used are not particularly limited. For example, silane coupling agents such as aminosilane, epoxysilane, acrylicsilane, mercaptosilane, vinylsilane, ureidosilane, acid anhydride-functionalized silane, and sulfidesilane can be used. One silane coupling agent may be used alone, or two or more may be used in combination. Among these, epoxysilane (i.e., a compound containing both an epoxy moiety and a group that generates a silanol group by hydrolysis in one molecule) or acid anhydride-functionalized silane (i.e., a compound containing both an acid anhydride group and a group that generates a silanol group by hydrolysis in one molecule) is preferred. The group on the opposite side of the silane coupling agent can bond to polymer A or polymer B or become more compatible with the polymer, thereby further improving the adhesion of the resin film or pattern formed from the photosensitive resin composition to the substrate.

[0102] Examples of aminosilanes include bis(2-hydroxyethyl)-3-aminopropyltriethoxysilane, γ-aminopropyltriethoxysilane, γ-aminopropyltrimethoxysilane, γ-aminopropylmethyldiethoxysilane, γ-aminopropylmethyldimethoxysilane, N-β(aminoethyl)γ-aminopropyltrimethoxysilane, N-β(aminoethyl)γ-aminopropyltriethoxysilane, N-β(aminoethyl)γ-aminopropylmethyldimethoxysilane, N-β(aminoethyl)γ-aminopropylmethyldiethoxysilane, or N-phenyl-γ-aminopropyltrimethoxysilane.

[0103] Examples of epoxysilanes include γ-glycidoxypropyltrimethoxysilane, γ Examples include glycidoxypropylmethyldiethoxysilane, or β-(3,4-epoxycyclohexyl)ethyltrimethoxysilane, γ-glycidylpropyltrimethoxysilane, etc.

[0104] Examples of acrylicsilanes include γ-(methacryloxypropyl)trimethoxysilane, γ-(methacryloxypropyl)methyldimethoxysilane, or γ-(methacryloxypropyl)methyldiethoxysilane.

[0105] Examples of mercaptosilanes include 3-mercaptopropyltrimethoxysilane. Examples of vinylsilanes include vinyltris(β-methoxyethoxy)silane, vinyltriethoxysilane, or vinyltrimethoxysilane.

[0106] Examples of ureidosilanes include 3-ureidopropyltriethoxysilane. Examples of acid anhydride-functionalized silanes include 3-trimethoxysilylpropyl succinic anhydride.

[0107] Examples of sulfidosilanes include bis(3-(triethoxysilyl)propyl) disulfide or bis(3-(triethoxysilyl)propyl) tetrasulfide.

[0108] When using adhesion enhancers, you may use only one type, or two or more types in combination. The amount of adhesion enhancer is typically 0.01 to 10 parts by mass, preferably 0.05 to 5 parts by mass, when the total solid content of the photosensitive resin composition is considered to be 100 parts by mass. It is believed that this range allows for sufficient adhesion, which is the effect of the adhesion enhancer, while maintaining a balance with other performance characteristics.

[0109] (solvent) The photosensitive resin composition according to this embodiment may contain a urea compound or an acyclic amide compound as a solvent. Preferably, the solvent contains a urea compound. This improves the adhesion between the cured product of the photosensitive resin composition and metals such as Al and Cu.

[0110] In this specification, a urea compound refers to a compound containing a urea bond, i.e., a urea bond. An amide compound refers to a compound containing an amide bond, i.e., an amide. Specifically, amides include primary amides, secondary amides, and tertiary amides.

[0111] Furthermore, in this embodiment, an acyclic structure means that the compound does not contain cyclic structures such as carbocyclic rings, inorganic rings, or heterocyclic rings. Examples of compounds that do not contain cyclic structures include linear structures and branched structures.

[0112] For urea compounds and acyclic amide compounds, those with a large number of nitrogen atoms in their molecular structure are preferred. Specifically, it is preferable that the molecular structure contains two or more nitrogen atoms. This increases the number of lone pairs of electrons. Therefore, adhesion to metals such as Al and Cu can be improved.

[0113] Specific structural examples of urea compounds include cyclic and acyclic structures. Of the above examples, an acyclic structure is preferred for the urea compound. This improves the adhesion between the cured photosensitive resin composition and metals such as Al and Cu. The reason for this is presumed to be as follows: Acyclic urea compounds are thought to form coordination bonds more easily than cyclic urea compounds. This is because acyclic urea compounds have fewer restrictions on molecular motion and a greater degree of freedom in molecular structure deformation compared to cyclic urea compounds. Therefore, when an acyclic urea compound is used, strong coordination bonds can be formed, improving adhesion.

[0114] Examples of urea compounds include tetramethylurea (TMU), 1,3-dimethyl-2-imidazolidinone, N,N-dimethylacetamide, tetrabutylurea, N,N'-dimethylpropyleneurea, 1,3-dimethoxy-1,3-dimethylurea, N,N'-diisopropyl-O-methylisourea, O,N,N'-triisopropylisourea, O-tert-butyl-N,N'-diisopropylisourea, O-ethyl-N,N'-diisopropylisourea, and O-benzyl-N,N'-diisopropylisourea. One or more of the above specific examples of urea compounds can be used in combination. As the urea compound, it is preferable to use one or more selected from the group consisting of tetramethylurea (TMU), tetrabutylurea, 1,3-dimethoxy-1,3-dimethylurea, N,N'-diisopropyl-O-methylisourea, O,N,N'-triisopropylisourea, O-tert-butyl-N,N'-diisopropylisourea, O-ethyl-N,N'-diisopropylisourea, and O-benzyl-N,N'-diisopropylisourea, with tetramethylurea (TMU) being more preferable. This allows for the formation of strong coordination bonds and improves adhesion.

[0115] Examples of acyclic amide compounds include 3-methoxy-N,N-dimethylpropanamide, N,N-dimethylformamide, N,N-dimethylpropionamide, N,N-diethylacetamide, 3-butoxy-N,N-dimethylpropanamide, and N,N-dibutylformamide. The photosensitive resin composition according to this embodiment may contain, as a solvent, a urea compound, an acyclic amide compound, or a solvent that does not contain a nitrogen atom.

[0116] Examples of solvents that do not contain nitrogen atoms include ether-based solvents, acetate-based solvents, alcohol-based solvents, ketone-based solvents, lactone-based solvents, carbonate-based solvents, sulfone-based solvents, ester-based solvents, and aromatic hydrocarbon-based solvents. One or more of the above specific examples can be used as solvents that do not contain nitrogen atoms.

[0117] Examples of the above-mentioned ether-based solvents include propylene glycol monomethyl ether (PGME), propylene glycol monoethyl ether, ethylene glycol monoethyl ether, diethylene glycol dimethyl ether, diethylene glycol monoethyl ether, diethylene glycol, ethylene glycol diethyl ether, diethylene glycol diethyl ether, diethylene glycol dibutyl ether, dipropylene glycol monomethyl ether, and 1,3-butylene glycol-3-monomethyl ether.

[0118] Examples of the acetate-based solvents mentioned above include propylene glycol monomethyl ether acetate (PGMEA), methyl lactate, ethyl lactate, butyl lactate, and methyl-1,3-butylene glycol acetate.

[0119] Examples of the above-mentioned alcohol-based solvents include tetrahydrofurfuryl alcohol, benzyl alcohol, 2-ethylhexanol, butanediol, and isopropyl alcohol. Examples of the ketone solvents mentioned above include cyclopentanone, cyclohexanone, diacetone alcohol, and 2-heptanone. Examples of the lactone-based solvents mentioned above include γ-butyrolactone (GBL) and γ-valerolactone. Examples of the carbonate-based solvents mentioned above include ethylene carbonate and propylene carbonate. Examples of the above-mentioned sulfone-based solvents include dimethyl sulfoxide (DMSO) and sulfolane. Examples of the ester solvents mentioned above include methyl pyruvate, ethyl pyruvate, and methyl-3-methoxypropionate. Examples of the above-mentioned aromatic hydrocarbon solvents include mesitylene, toluene, and xylene. Of the solvents mentioned above, the more preferred solvents are PGMEA and cyclopentanone. Using these solvents can improve the solubility of polymer A (polynorbornene) and polymer B (polyimide).

[0120] The lower limit of the content of urea compounds and acyclic amide compounds in the solvent is preferably 10 parts by mass or more, more preferably 20 parts by mass or more, even more preferably 30 parts by mass or more, even more preferably 50 parts by mass or more, and especially preferably 70 parts by mass or more, when the solvent is 100 parts by mass. This further improves the adhesion between the cured product of the photosensitive resin composition and metals such as Al and Cu.

[0121] Furthermore, the lower limit of the content of urea compounds and acyclic amide compounds in the solvent can be, for example, 100 parts by mass or less, when the solvent is 100 parts by mass. From the viewpoint of improving adhesion, it is preferable that the solvent contains a high amount of urea compounds and acyclic amide compounds.

[0122] (Surfactants) The photosensitive resin composition according to this embodiment may further contain a surfactant.

[0123] The surfactants are not limited to, but specifically include polyoxyethylene alkyl ethers such as polyoxyethylene lauryl ether, polyoxyethylene stearyl ether, and polyoxyethylene oleyl ether; polyoxyethylene aryl ethers such as polyoxyethylene octylphenyl ether and polyoxyethylene nonylphenyl ether; nonionic surfactants such as polyoxyethylene dialkyl esters such as polyoxyethylene dilaurate and polyoxyethylene distearate; F-Top EF301, F-Top EF303, F-Top EF352 (manufactured by Shin Akita Chemical Co., Ltd.), Megafac F171, Megafac F172, Megafac F173, Megafac F177, Megafac F444, Megafac F470, Examples include fluorinated surfactants commercially available under names such as Megafac F471, Megafac F475, Megafac F482, Megafac F477 (manufactured by DIC Corporation), Florard FC-430, Florard FC-431, Novec FC4430, Novec FC4432 (manufactured by 3M Japan), Surflon S-381, Surflon S-382, Surflon S-383, Surflon S-393, Surflon SC-101, Surflon SC-102, Surflon SC-103, Surflon SC-104, Surflon SC-105, Surflon SC-106 (manufactured by AGC Seimi Chemical Co., Ltd.); organosiloxane copolymer KP341 (manufactured by Shin-Etsu Chemical Co., Ltd.); and (meth)acrylic acid copolymer Polyflow No. 57 and 95 (manufactured by Kyoeisha Chemical Co., Ltd.).

[0124] Among these, it is preferable to use a fluorinated surfactant having a perfluoroalkyl group. As a fluorinated surfactant having a perfluoroalkyl group, it is preferable to use one or more selected from the above specific examples: Megafac F171, Megafac F173, Megafac F444, Megafac F470, Megafac F471, Megafac F475, Megafac F482, Megafac F477 (manufactured by DIC Corporation), Surflon S-381, Surflon S-383, Surflon S-393 (manufactured by AGC Seimi Chemical Co., Ltd.), Novec FC4430, and Novec FC4432 (manufactured by 3M Japan).

[0125] Furthermore, silicone-based surfactants (such as polyether-modified dimethylsiloxane) can also be preferably used as surfactants. Specific examples of silicone-based surfactants include the SH series, SD series, and ST series from Toray Dow Corning, the BYK series from BIC Chemie Japan, the KP series from Shin-Etsu Chemical Co., Ltd., the Disform® series from NOF Corporation, and the TSF series from Toshiba Silicone Co., Ltd.

[0126] The upper limit of the surfactant content in the photosensitive resin composition is preferably 1% by mass (10,000 ppm) or less, more preferably 0.5% by mass (5,000 ppm) or less, and even more preferably 0.1% by mass (1,000 ppm) or less, relative to the total amount of the photosensitive resin composition (including the solvent).

[0127] Furthermore, there is no particular lower limit for the surfactant content in the photosensitive resin composition, but from the viewpoint of obtaining sufficient effects from the surfactant, for example, it should be 0.001% by mass (10 ppm) or more relative to the total amount of the photosensitive resin composition (including the solvent). By appropriately adjusting the amount of surfactant, it is possible to improve application properties and the uniformity of the coating film while maintaining other performance characteristics.

[0128] (Antioxidant) The photosensitive resin composition according to this embodiment may further contain an antioxidant. One or more antioxidants selected from phenol-based antioxidants, phosphorus-based antioxidants, and thioether-based antioxidants can be used. The antioxidant can suppress the oxidation of the resin film formed by the photosensitive resin composition.

[0129] Examples of phenol-based antioxidants include pentaerythrityl-tetrakis[3-(3,5-di-t-butyl-4-hydroxyphenyl)propionate], 3,9-bis{2-[3-(3-t-butyl-4-hydroxy-5-methylphenyl)propionyloxy]-1,1-dimethylethyl}2,4,8,10-tetraoxaspiro[5,5]undecane, octadecyl-3-(3,5-di-t-butyl-4-hydroxyphenyl)propionate, and 1,6-hexanediol-bis[3-(3,5-di-t-butyl-4-hydroxyphenyl)propionate [(3,5-di-t-butyl-4-hydroxybenzyl)benzene], 1,3,5-trimethyl-2,4,6-tris(3,5-di-t-butyl-4-hydroxybenzyl)benzene, 2,6-di-t-butyl-4-methylphenol, 2,6-di-t-butyl-4-ethylphenol, 2,6-diphenyl-4-octadecyloxyphenol, stearyl(3,5-di-t-butyl-4-hydroxyphenyl)propionate, distearyl(3,5-di-t-butyl-4-hydroxybenzyl)phosphonate, thiodiethylene glycol bis[(3,5-di-t-butyl-4-hydroxyphenyl)propionate 4,4'-thiobis(6-t-butyl-m-cresol), 2-octylthio-4,6-di(3,5-di-t-butyl-4-hydroxyphenoxy)-s-triazine, 2,2'-methylenebis(4-methyl-6-t-butyl-6-butylphenol), 2,-2'-methylenebis(4-ethyl-6-t-butylphenol), bis[3,3-bis(4-hydroxy-3-t-butylphenyl)butyric acid] glycol ester, 4,4'-butylidenebis(6-t-butyl-m-cresol), 2,2'-ethylidenebis(4,6-di- t-butylphenol), 2,2'-ethylidenebis(4-s-butyl-6-t-butylphenol), 1,1,3-tris(2-methyl-4-hydroxy-5-t-butylphenyl)butane, bis[2-t-butyl-4-methyl-6-(2-hydroxy-3-t-butyl-5-methylbenzyl)phenyl]terephthalate, 1,3,5-tris(2,6-dimethyl-3-hydroxy-4-t-butylbenzyl)isocyanurate, 1,3,5-tris(3,5-di-t-butyl-4-hydroxybenzyl)-2,4,6-trimethylbenzene, 1,3,5-Tris[(3,5-di-t-butyl-4-hydroxyphenyl)propionyloxyethyl]isocyanurate, tetrakis[methylene-3-(3,5-di-t-butyl-4-hydroxyphenyl)propionate]methane, 2-t-butyl-4-methyl-6-(2-acryloyloxy-3-t-butyl-5-methylbenzyl)phenol, 3,9-bis(1,1-dimethyl-2-hydroxyethyl)-2,4-8,10-tetraoxaspiro[5,5] Undecane-bis[β-(3-t-butyl-4-hydroxy-5-methylphenyl)propionate], triethyleneglycol-bis[β-(3-t-butyl-4-hydroxy-5-methylphenyl)propionate], 1,1'-bis(4-hydroxyphenyl)cyclohexane, 2,2'-methylenebis(4-methyl-6-t-butylphenol), 2,2'-methylenebis(4-ethyl-6-t-butylphenol), 2,2'-methylenebis(6-(1 -methylcyclohexyl)-4-methylphenol), 4,4'-butylidenebis(3-methyl-6-t-butylphenol), 3,9-bis(2-(3-t-butyl-4-hydroxy-5-methylphenylpropionyloxy)1,1-dimethylethyl)-2,4,8,10-tetraoxaspiro(5,5)undecane, 4,4'-thiobis(3-methyl-6-t-butylphenol), 4,4'-bis(3,5-di-t-butyl-4-hydroxybenzyl) Examples include ruphaide, 4,4'-thiobis(6-t-butyl-2-methylphenol), 2,5-di-t-butylhydroquinone, 2,5-di-t-amylhydroquinone, 2-t-butyl-6-(3-t-butyl-2-hydroxy-5-methylbenzyl)-4-methylphenyl acrylate, 2,4-dimethyl-6-(1-methylcyclohexyl, styrenelated phenol, 2,4-bis((octylthio)methyl)-5-methylphenol, etc.

[0130] Examples of phosphorus-based antioxidants include bis(2,6-di-t-butyl-4-methylphenyl)pentaerythritol diphosphite, tris(2,4-di-t-butylphenyl phosphite), tetrakis(2,4-di-t-butyl-5-methylphenyl)-4,4'-biphenylenediphosphonite, 3,5-di-t-butyl-4-hydroxybenzylphosphonate-diethyl ester, bis-(2,6-dicumylphenyl)pentaerythritol diphosphite, and 2,2-methylenebi. Examples include s(4,6-di-t-butylphenyl)octyl phosphite, tris(mixed mono- and di-nonylphenyl phosphite), bis(2,4-di-t-butylphenyl)pentaerythritol diphosphite, bis(2,6-di-t-butyl-4-methoxycarbonylethylphenyl)pentaerythritol diphosphite, and bis(2,6-di-t-butyl-4-octadecyloxycarbonylethylphenyl)pentaerythritol diphosphite.

[0131] Examples of thioethyl antioxidants include dilauryl-3,3'-thiodipropionate, bis(2-methyl-4-(3-n-dodecyl)thiopropionyloxy)-5-t-butylphenyl) sulfide, distearyl-3,3'-thiodipropionate, and pentaerythritol-tetrakis(3-lauryl)thiopropionate.

[0132] (Filler) The photosensitive resin composition according to this embodiment may further contain a filler. As the filler, an appropriate filler can be selected according to the mechanical and thermal properties required for the resin film made of the photosensitive resin composition. Examples of fillers include inorganic fillers and organic fillers.

[0133] Examples of the inorganic fillers mentioned above include silica such as molten crushed silica, molten spherical silica, crystalline silica, secondary aggregated silica, and fine silica; metal compounds such as alumina, silicon nitride, aluminum nitride, boron nitride, titanium oxide, silicon carbide, aluminum hydroxide, magnesium hydroxide, and titanium white; talc; clay; mica; and glass fibers. One or more of the above specific examples of inorganic fillers can be used in combination.

[0134] Examples of the above-mentioned organic fillers include organosilicone powder and polyethylene powder. One or more of the above-mentioned organic fillers can be used in combination.

[0135] (Preparation of photosensitive resin composition) The method for preparing the photosensitive resin composition in this embodiment is not limited, and known methods can be used depending on the components contained in the photosensitive resin composition. For example, the above components can be prepared by mixing and dissolving them in a solvent.

[0136] (Photosensitive resin composition, cured film) The photosensitive resin composition according to this embodiment is used by coating the photosensitive resin composition onto a surface having a metal such as Al or Cu, then pre-baking and drying to form a resin film, then exposing and developing the resin film to a desired shape, and finally post-baking to cure the resin film and form a cured film.

[0137] When producing the above permanent film, pre-baking conditions can include, for example, heat treatment at a temperature of 50°C to 150°C for 30 seconds to 1 hour. Post-baking conditions can include, for example, heat treatment at a temperature of 150°C to 250°C for 30 minutes to 10 hours.

[0138] The viscosity of the photosensitive resin composition according to this embodiment can be appropriately set according to the desired thickness of the resin film. The viscosity of the photosensitive resin composition can be adjusted by adding a solvent. When adjusting the viscosity, it is necessary to keep the content of urea compounds and acyclic amide compounds in the solvent constant.

[0139] The upper limit of the viscosity of the photosensitive resin composition according to this embodiment may be, for example, 5000 mPa·s or less, 4000 mPa·s or less, or 3000 mPa·s or less. The lower limit of the viscosity of the photosensitive resin composition according to this embodiment may be, for example, 10 mPa·s or more, or 50 mPa·s or more, depending on the desired thickness of the resin film.

[0140] The film obtained from the photosensitive resin composition of this embodiment has an elongation rate measured by tensile testing using a Tensilon tester, with a maximum value of 10-200%, preferably 20-150%, and an average value of 1-150%, preferably 2-120%. The film obtained from the photosensitive resin composition of this embodiment can have a tensile strength of 30 to 300 MPa, preferably 50 to 200 MPa.

[0141] Thus, the photosensitive resin composition of this embodiment can provide cured products such as films with excellent mechanical strength. The reason for this is not clear, but it is presumed to be due to the excellent properties of the rigid polyimide of the present invention.

[0142] The film made from the photosensitive resin composition of this embodiment exhibits excellent low dielectric loss tangent, with a dielectric loss tangent (tanδ) of 0.008 or less when measured at a frequency of 10 GHz, preferably 0.007 or less, and more preferably 0.006 or less.

[0143] The film made from the photosensitive resin composition of this embodiment has suppressed curing shrinkage, and its linear thermal expansion coefficient (CTE) can be 200 ppm / °C or less, preferably 150 ppm / °C or less.

[0144] In this embodiment, it is preferable that the polyimide contained in polymer B does not contain halogen atoms. As a result, the cured product, such as a film made from the photosensitive resin composition, exhibits excellent hydrolysis resistance and suppresses the deterioration of mechanical properties. Specifically, a cured product (film) made from a photosensitive resin composition containing polymer A and polymer B containing a halogen atom-free polyimide exhibits excellent hydrolysis resistance. Even after a HAST test (unsaturated pressurized steam test) conducted at a temperature of 130°C and a relative humidity of 85%RH for 96 hours, the decrease in the elongation rate (maximum value) expressed by the following formula is 20% or less, preferably 15% or less, and more preferably 12% or less. [(Growth rate before the exam - Growth rate after the exam) / Growth rate before the exam)] × 100

[0145] (Application) The photosensitive resin composition (negative-type photosensitive resin composition) of this embodiment is used to form resin films for semiconductor devices such as permanent films and resists. Among these, it is preferable to use it in applications where a permanent film is used, from the viewpoint of achieving a good balance between improving the adhesion between the photosensitive resin composition and the Al pad after pre-baking and suppressing the generation of residue of the photosensitive resin composition during development, from the viewpoint of improving the adhesion between the cured film of the photosensitive resin composition after post-baking and the metal, and in addition, from the viewpoint of improving the chemical resistance of the photosensitive resin composition after post-baking.

[0146] In this embodiment, the resin film includes a cured film of a photosensitive resin composition. That is, the resin film according to this embodiment is obtained by curing a photosensitive resin composition.

[0147] The above-mentioned permanent film is composed of a resin film obtained by pre-baking, exposing, and developing a photosensitive resin composition, patterning it into a desired shape, and then curing it by post-baking. The permanent film can be used as a protective film, interlayer film, or dam material for semiconductor devices.

[0148] The above-mentioned resist is composed of a resin film obtained by, for example, applying a photosensitive resin composition to an object to be masked by the resist using methods such as spin coating, roll coating, flow coating, dip coating, spray coating, or doctor coating, and then removing the solvent from the photosensitive resin composition.

[0149] An example of a semiconductor device according to this embodiment is shown in Figure 1. The semiconductor device 100 according to this embodiment may be a semiconductor device comprising the resin film described above. Specifically, one or more of the group consisting of the passivation film 32, insulating layer 42, and insulating layer 44 in the semiconductor device 100 may be a resin film containing the cured product of this embodiment. Here, it is preferable that the resin film is the permanent film described above.

[0150] The semiconductor device 100 is, for example, a semiconductor chip. In this case, for example, a semiconductor package is obtained by mounting the semiconductor device 100 on a wiring board via bumps 52.

[0151] The semiconductor device 100 comprises a semiconductor substrate on which semiconductor elements such as transistors are provided, and a multilayer wiring layer (not shown) provided on the semiconductor substrate. The uppermost layer of the multilayer wiring layer is provided with an interlayer insulating film 30 and an uppermost wiring 34 provided on the interlayer insulating film 30. The uppermost wiring 34 is made of, for example, aluminum Al. A passivation film 32 is also provided on the interlayer insulating film 30 and the uppermost wiring 34. An opening is provided in a part of the passivation film 32 that exposes the uppermost wiring 34.

[0152] A rewiring layer 40 is provided on the passivation film 32. The rewiring layer 40 includes an insulating layer 42 provided on the passivation film 32, rewiring 46 provided on the insulating layer 42, and an insulating layer 44 provided on the insulating layer 42 and the rewiring 46. The insulating layer 42 has openings formed therein that connect to the uppermost wiring 34. The rewiring 46 is formed on the insulating layer 42 and within the openings provided in the insulating layer 42 and is connected to the uppermost wiring 34. The insulating layer 44 has openings that connect to the rewiring 46.

[0153] Bumps 52 are formed within the openings provided in the insulating layer 44, for example, via a UBM (Under Bump Metallurgy) layer 50. The semiconductor device 100 is connected to a wiring board or the like via the bumps 52. Although embodiments of the present invention have been described above, these are merely examples, and various other configurations can be adopted as long as they do not impair the effects of the present invention. [Examples]

[0154] The present invention will be described in more detail below with reference to examples, but the present invention is not limited thereto. Unless otherwise specified in these examples, all parts and percentages are given by weight, all temperatures are in degrees Celsius, and pressures are atmospheric pressure or near atmospheric pressure.

[0155] [Synthesis Example 1] (Synthesis of maleic anhydride-modified norbornene monomer (DMMIBuNB, 1-[4-(5-2-norbornyl)butyl]-3,4-dimethylpyrrole-2,5-dione)) In a 1 L four-necked round-bottom flask (RBF) equipped with a thermowell, a condenser with a nitrogen inlet, an addition funnel, and a mechanical stirrer, 200 mL of toluene was added, followed by DMMI potassium (35 g, 0.21 mol) and 18-crown-6 (5.7 g, 0.021 mol, 10 mol%), with stirring. Endo-exo-NBBuBr (45 g, 0.20 mol) in 200 mL of toluene was added to the addition funnel over 5 minutes. The mixture was heated to 100°C, and an off-white slurry was observed. The mixture was stirred for a further 6.5 hours, and the color changed from the initially observed off-white to dark green, and then to reddish-brown. The reaction was monitored by GC, and it was found that the reaction was complete with 73.6% product and 15.6% unreacted endo-exo-NBBuBr. Next, the reaction mixture was cooled to room temperature, quenched with 250 mL of water, and then diluted with 150 mL of toluene. The aqueous layer was extracted with CH2Cl2 (2 × 200 mL), the organic layer was washed with brine, dried over Na2SO4, filtered, and evaporated to obtain 55 g of crude product as brown oil. The crude product was adsorbed onto 55 g of SiO2 and eluted by chromatography on 330 g of SiO2 using pentane (3 L), pentane (5 L) with 2% Â, heptane (3 L) with 3% Â, and heptane (2 L) with 4% Â. From the concentrated and purified fraction, 31 g of product was obtained as a colorless viscous oil (yield 58%) with a purity of 99.3% by HPLC, and 7.0 g of product (yield 13.1%) from another fraction was obtained with a purity of 99.09% by HPLC. The combined yield for the reaction was 71%. 1 1H-NMR and MS were consistent with the structure of DMMIBuNB. The reaction equation is shown below.

[0156] [ka]

[0157] (Synthesis of polymer (DMMI-PNB(1))) In a nitrogen-purged reaction vessel, 596 g of 1-[4-(5-2-norbornyl)butyl]-3,4-dimethylpyrrole-2,5-dione) obtained by the above method, 1,849 g of toluene, and 457 g of ethyl acetate were charged. Furthermore, 66 ml of a toluene solution of 10 wt% (toluene)bis(perfluorophenyl)nickel was added, and the reaction was carried out at 49°C for 2 hours. After 2 hours, the reaction was stopped by adding 11 g of water to obtain a polymer solution. The conversion rate to polymer was 99%. To 100 parts by weight of the prepared polymer solution, 150 g of ethyl acetate, 463 g of isopropanol, 254 g of acetic acid, 481 g of hydrogen peroxide solution (30%), and 601 g of water were added, and the mixture was stirred at 160 rpm while heating to 50°C. After reaching 50°C, stirring was continued for another 30 minutes. After 30 minutes, the stirring speed was reduced to 50 rpm, 154 g of isopropanol was added, and the mixture was stirred for 10 minutes, then allowed to stand at 50°C for another 30 minutes. After standing, the mixture was separated into an organic phase and an aqueous phase, and the aqueous phase was discarded. The resulting resin solution was reprecipitated with MeOH, filtered, and vacuum-dried at 50°C to obtain 545 g of polymer (DMMI-PNB(1)). The Mw was 100,000.

[0158] [Synthesis Example 2] (Synthesis of maleic anhydride-modified norbornene monomer (DMMIBuNB, 1-[4-(5-2-norbornyl)butyl]-3,4-dimethylpyrrole-2,5-dione)) In a 500 mL round-bottom flask, dimethyl maleic anhydride (42.6 g, 0.34 mol) was dissolved in toluene (300 mL) at room temperature. To remove oxygen, the solution was placed under a nitrogen atmosphere. The reaction flask was placed in an ice bath to prevent excessive heating due to the exothermic reaction. Once the dimethyl maleic anhydride was dissolved, a dropping funnel containing 5-norbornene-2-butylamine (49.6 g, 0.30 mol) was attached, and the norbornene compound was added dropwise to the reaction flask over 3 hours. The dropping funnel was removed, and a Dean-Stark tube and reflux condenser were attached to the flask. The solution was heated and refluxed in an oil bath set to 125°C, and the reactants were stirred at that temperature for 18 hours. During this time, approximately 6 mL of water was collected in the Dean-Stark tube. The flask was removed from the oil bath and cooled to room temperature. The toluene solvent was removed using an evaporator to obtain a yellow oily substance. The crude product was placed on a flash chromatography column (250 g of silica gel) and eluted using a solvent mixture of 1.7 liters of cyclohexane / ethyl acetate (95 / 5 wt ratio). The eluent was removed using an evaporator, and then dried under vacuum at 45°C for 18 hours to obtain 80.4 g (yield 92.7%) of the target product. The reaction equation is shown below.

[0159] [ka]

[0160] (Synthesis of polymer (DMMI-PNB(2))) After venting a reaction vessel of appropriate size, equipped with a stirrer and condenser, with nitrogen for 1 hour, 1-[4-(5-2-norbornyl)butyl]-3,4-dimethylpyrrole-2,5-dione (NBBuDMMI) (24.60 g, 90 mmol) and triethylsilane (3.14 g, 27 mmol) were added. Further, cyclopentyl methyl ether (CPME) (16.04 g) and ethyl acetate (EA) (1.98 g) were added to obtain the reaction solution. The reaction solution was heated to 70°C with stirring under a nitrogen flow (50 mL / min). A solution was prepared by dissolving the catalyst (palladium(II)(acetonitrile)bis(triisopropylphosphine)acetatetetrakis(2,3,4,5,6-pentafluorophenyl) borate, Pd-1206) (0.0434 g) and the co-catalyst (N,N-dimethylanilinium tetrakis(pentafluorophenyl) borate, DANFABA) (0.0288 g) in ethyl acetate (EA) (3.37 g). These solutions were then added to the reaction solution in a molar ratio of NBBuDMMI:catalyst:co-catalyst = 2500:1:1. Polymerization was carried out at 70°C for 3 hours, and after polymerization, the reaction was stopped by allowing it to cool. The obtained polymerization solution was diluted with tetrahydrofuran to prepare a dilution, and then the dilution was added dropwise to a methanol solution to precipitate a white solid. The obtained white solid was collected and vacuum-dried at 50°C to obtain 20.02 g of the polymer (DMMI-PNB(2)). The Mw was 6000.

[0161] The following compounds were used in synthesis examples 3-6. 4,4'-(hexafluoroisopropylidene)diphthalic anhydride (hereinafter also referred to as 6FDA), represented by the following formula

[0162] [ka]

[0163] The following formula represents 2,2'-bis(trifluoromethyl)benzidine (hereinafter also referred to as TFMB):

[0164] [ka]

[0165] The following formula represents 4-[4-(1,3-dioxoisobenzofuran-5-ylcarbonyloxy)-2,3,5-trimethylphenyl]-2,3,6-trimethylphenyl 1,3-dioxoisobenzofuran-5-carboxylate (hereinafter also referred to as TMPBP-TME)

[0166] 4,4-diamino-3,3-diethyl-5,5-dimethyldiphenylmethane (hereinafter also referred to as MED-J), represented by the following formula [ka]

[0167] A mixture of 1-(4-aminophenyl)-1,3,3-trimethylphenylindan-6-amine and 1-(4-aminophenyl)-1,3,3-trimethylphenylindan-5-amine (hereinafter also referred to as TMDA) represented by the following formula. [ka]

[0168] 9,9-bis(3-methyl-4-aminophenyl)fluorene (hereinafter also referred to as BTFL), represented by the following formula [ka]

[0169] [ka]

[0170] [Synthesis Example 3] (Synthesis of polymer (DMMI-PI(1))) First, 16.09 g (50.2 mmol) of TFMB, 11.05 g (24.9 mmol) of 6FDA, and 15.39 g (24.9 mmol) of TMPBP-TME were placed in a reaction vessel of appropriate size equipped with a stirrer and condenser. Then, 99.24 g of γ-butyrolactone (hereinafter also referred to as GBL) was added to the reaction vessel. After aeration with nitrogen for 10 minutes, the temperature was raised to 60°C while stirring, and the reaction was carried out for 1 hour. Prior to this, a solution was prepared by dissolving 0.38 g (3.0 mmol) of dimethyl maleic anhydride in 0.78 g of γ-butyrolactone. This solution was added to the reaction vessel, and the reaction was carried out for another 30 minutes. The reaction was then carried out at 175°C for 3 hours to polymerize the diamine and acid anhydride, and a polymerization solution was prepared with sealed ends. The obtained polymerization solution was diluted with acetone to prepare a diluent, and then the diluent was added dropwise to a methanol solution to precipitate a white solid. The obtained white solid was collected and vacuum-dried at 120°C to obtain 34.78 g of the polymer (DMMI-PI(1)) represented by the following formula. GPC analysis of the polymer revealed a weight-average molecular weight (Mw) of 76991, a polydispersity (weight-average molecular weight Mw / number-average molecular weight Mn) of 2.06, and a end-capacity of 93%. In the formula, m:n ≈ 1:1.

[0171] [ka]

[0172] IR measurements of the polymer yielded values ​​of 1480, 1550, and 1670 cm⁻¹. -1 The peaks originating from the nearby amide group had disappeared, confirming that imidation was complete.

[0173] [Synthesis Example 4] (Synthesis of polymer (DMMI-PI(2))) First, 43.99 g (155.8 mmol) of MED-J and 89.22 g (144.2 mmol) of TMPBP-TME were placed in a reaction vessel of appropriate size equipped with a stirrer and condenser. Then, 399.64 g of γ-butyrolactone (hereinafter also referred to as GBL) was added to the reaction vessel. After aeration with nitrogen for 10 minutes, the temperature was raised to 60°C while stirring, and the reaction was carried out for 1 hour. Prior to this, a solution was prepared by dissolving 8.73 g (69.2 mmol) of dimethyl maleic anhydride in 26.19 g of gamma butyrolactone. This solution was added to the reaction vessel, and the reaction was carried out for another 30 minutes. The reaction was then carried out at 175°C for 3 hours to polymerize the diamine and acid anhydride, and a polymerization solution was prepared with sealed ends. The obtained polymerization solution was diluted with tetrahydrofuran to prepare a diluent, and then the diluent was added dropwise to a methanol solution to precipitate a white solid. The obtained white solid was collected and vacuum-dried at 80°C to obtain 125.88 g of the polymer (DMMI-PI(2)) represented by the following formula. GPC analysis of the polymer revealed a weight-average molecular weight (Mw) of 74,000, a polydispersity (weight-average molecular weight Mw / number-average molecular weight Mn) of 2.62, and a end-capacitation rate of 65%. [ka]

[0174] [Synthesis Example 5] (Synthesis of polymer (DMMI-PI(3))) First, 7.17 g (25.4 mmol) of MED-J, 6.76 g (25.4 mmol) of TMDA, and 30.47 g (49.3 mmol) of TMPBP-TME were placed in a reaction vessel of appropriate size equipped with a stirrer and condenser. Then, 159.82 g of γ-butyrolactone (hereinafter also referred to as GBL) was added to the reaction vessel. After aeration with nitrogen for 10 minutes, the temperature was raised to 60°C while stirring and the reaction was carried out for 1 hour. Prior to this, a solution was prepared by dissolving 1.12 g (8.9 mmol) of dimethyl maleic anhydride in 4.47 g of gamma butyrolactone. This solution was added to the reaction vessel and the reaction was carried out for another 30 minutes. The reaction was then carried out at 175°C for 3 hours to polymerize the diamine and acid anhydride and to prepare a polymerization solution with sealed ends. The obtained polymerization solution was diluted with tetrahydrofuran to prepare a dilution, and then the dilution was added dropwise to a methanol solution to precipitate a white solid. The obtained white solid was collected and vacuum-dried at 80°C to obtain 40.62 g of polymer (DMMI-PI(3)). GPC analysis of the polymer revealed a weight-average molecular weight (Mw) of 77,000, a polydispersity (weight-average molecular weight Mw / number-average molecular weight Mn) of 2.07, and a end-capacitation rate of 98%.

[0175] [Synthesis Example 6] (Synthesis of polymer (DMMI-PI(4))) First, 7.17 g (25.4 mmol) of MED-J, 9.55 g (25.4 mmol) of BTFL, and 30.47 g (49.3 mmol) of TMPBP-TME were placed in a reaction vessel of appropriate size equipped with a stirrer and condenser. Then, 169.88 g of γ-butyrolactone (hereinafter also referred to as GBL) was added to the reaction vessel. After aeration with nitrogen for 10 minutes, the temperature was raised to 60°C while stirring and the reaction was carried out for 1 hour. Prior to this, a solution was prepared by dissolving 1.12 g (8.9 mmol) of dimethyl maleic anhydride in 4.47 g of gamma butyrolactone. This solution was added to the reaction vessel and the reaction was carried out for another 30 minutes. The reaction was then carried out at 175°C for 3 hours to polymerize the diamine and acid anhydride and to prepare a polymerization solution with sealed ends. The obtained polymerization solution was diluted with tetrahydrofuran to prepare a diluent, and then the diluent was added dropwise to a methanol solution to precipitate a white solid. The obtained white solid was collected and vacuum-dried at 80°C to obtain 43.69 g of polymer (DMMI-PI(4)). When the polymer was measured by GPC, the weight average molecular weight Mw was 83,000, the polydispersity (weight average molecular weight Mw / number average molecular weight Mn) was 2.10, and the end-capping rate was 86%.

[0176] In the following examples, the following components were used. · Photosensitizer: 1-chloro-4-propoxythioxanthone (manufactured by Lambson, SPEEDCURE CPTX (trade name)) · Solvent: Propylene glycol monomethyl ether acetate · Adhesion aid: 3-trimethoxysilylpropyl succinic anhydride (manufactured by Shin-Etsu Chemical Co., Ltd., trade name "X-12-967C")

[0177] [Examples 1 to 7, Comparative Examples 1 to 2] The components listed in Table 1 were mixed to prepare a photosensitive resin composition. The obtained photosensitive resin composition was spin-coated on the surface of a silicon wafer so that the film thickness after drying was 10 μm. After pre-baking at 120 °C for 3 minutes, it was exposed with a high-pressure mercury lamp at 2000 mJ / cm 2 , and then cured at 200 °C for 120 minutes in a nitrogen atmosphere to prepare a film. In Example 5, a film was prepared in the same manner as in Example 1 except that pre-baking was performed at 150 °C for 3 minutes and the exposure amount was changed to 800 mJ / cm 2 .

[0178] (Tensile strength, elongation rate and elastic modulus) A tensile test (stretching speed: 5 mm / min) was performed on test pieces (6.5 mm × 60 mm × 10 μm thick) cut out from the obtained film in an atmosphere of 23 °C. The tensile test was carried out using a tensile tester (Tensilon RTC-1210A) manufactured by Orientec Co., Ltd. Five test pieces were measured, and the stress at the breaking point averaged was taken as the strength. The tensile elongation rate was calculated from the broken distance and the initial distance, and the maximum value of the elongation rate was determined. The tensile elastic modulus was calculated from the initial gradient of the obtained stress-strain curve, and the averaged value was taken as the elastic modulus. The results are shown in Table 1. Furthermore, the test pieces cut from the obtained film were subjected to a HAST (Unsaturated Pressurized Steam Test) for 96 hours under conditions of 130°C and 85% RH relative humidity, and the maximum elongation was determined in the same manner as described above. The results are shown in Table 1.

[0179] (Coefficient of linear thermal expansion (CTE)) Strip-shaped test pieces measuring 13 mm in length and 4 mm in width were cut from the obtained film. Thermomechanical measurements were performed in tensile mode with a chuck distance of 10 mm, and the mean linear thermal expansion coefficient (CTE, 50°C to 100°C or 100°C to 200°C) was determined from the thermal expansion curve. The results are shown in Table 1.

[0180] (Glass transition temperature: Tg) Strip-shaped test pieces measuring 50 mm in length and 10 mm in width were cut from the obtained film. Dynamic viscoelasticity measurements were performed with a chuck distance of 20 mm, and the peak temperature of the obtained loss tangent (tanδ) was defined as the glass transition temperature (Tg). The measurement conditions were a nitrogen flow of 30 ml / min, an applied frequency of 1 Hz, and a heating rate of 5 °C / min. The results are shown in Table 1.

[0181] (Dielectric loss tangent Df) The photosensitive resin compositions of Examples 1-7 and Comparative Examples 1-2 were applied to substrates, dried at 120°C for 10 minutes, subjected to PLA exposure (540 mJ), and cured at 200°C for 2 hours under a nitrogen atmosphere to obtain a film with a thickness of 100 μm. The dielectric loss tangent of the obtained film at 10 GHz was measured using the cavity resonator method. The results are shown in Table 1.

[0182] [Table 1]

[0183] The results in Table 1 clearly show that the photosensitive resin composition of the present invention, when combined with a predetermined cyclic olefin resin and polyimide, yields a resin film with excellent low dielectric loss tangent and superior mechanical properties. Furthermore, it is inferred that the resin film also exhibits excellent hydrolysis resistance, suppressing the deterioration of mechanical properties and other characteristics. In addition, when a photosensitivity test was conducted on the photosensitive resin compositions of Examples 1 to 7, it was confirmed that holes with a diameter of 20 μm could be formed in all of them.

[0184] This application claims priority based on Japanese Patent Application No. 2021-021545 filed on February 15, 2021, and Japanese Patent Application No. 2021-105687 filed on June 25, 2021, and incorporates the entire disclosure thereof herein.

Explanation of Signs

[0185] 30 Interlayer Insulation Film 32 Passivation Film 34 Topmost Layer Wiring 40 Rewiring Layer 42 Insulation Layer 44 Insulation Layer 46 Rewiring 50 UBM Layer 52 Bump 100 Semiconductor Device

Claims

1. Polymer A having a constituent unit represented by the following general formula (a), Polymer B containing a polyimide having a group b represented by the following general formula (b), Includes, Furthermore, a photosensitive resin composition containing a photosensitizer. 【Chemistry 1】 (In general formula (a), R １ and R ２ Each of these independently represents a hydrogen atom or an alkyl group having 1 to 3 carbon atoms, Q １ This indicates a single bond or a divalent organic group, G １ G ２ , and G ３ Each of these independently represents a hydrogen atom, a substituted or unsubstituted hydrocarbon group having 1 to 30 carbon atoms, and m is 0, 1, or 2. 【Chemistry 2】 (In general formula (b), R ３ and R ４ each independently represents a hydrogen atom or an alkyl group having 1 to 3 carbon atoms, Q ２ represents a divalent organic group, and G ４ each independently represents a hydrogen atom, a substituted or unsubstituted hydrocarbon group having 1 to 30 carbon atoms. * represents a bond.)

2. Q １ The photosensitive resin composition according to claim 1, wherein the divalent organic group is an alkylene group having 1 to 8 carbon atoms or a (poly)alkylene glycol chain.

3. The photosensitive resin composition according to claim 1 or 2, wherein polymer B comprises a polyimide having a group b represented by the general formula (b) at both ends.

4. The Q of the general formula (b) ２ The photosensitive resin composition according to any one of claims 1 to 3, wherein the divalent organic group in is represented by the following general formula (b1). 【Transformation 3】 (In general formula (b1), R ５ and R ６ Each of the following independently represents a hydrogen atom, a C1-C4 haloalkyl group, a C1-C3 alkyl group, a C1-C3 alkoxy group, or a hydroxyl group. X represents a single bond, a C1-C4 alkylene group, a C1-C4 haloalkylene group, a divalent ether group derived from bisphenol A, a divalent ether group derived from bisphenol F, a divalent ether group derived from bisphenol S, or a divalent ether group derived from hexafluorobisphenol A. * indicates a bond.

5. Polymer (B) comprises a polyimide having at least one end a group c represented by the following general formula (c), The photosensitive resin composition according to claim 1 or 2, wherein in the polyimide contained in polymer (B), the ratio of the number of moles of group b to the total number of moles of group c (b / b+c) is 0.5 or more. 【Chemistry 4】 (In general formula (c), R ５ and R ６ Each independently represents a hydrogen atom, a C1-C4 haloalkyl group, a C1-C3 alkyl group, a C1-C3 alkoxy group, or a hydroxyl group, X represents a single bond, a C1-C4 alkylene group, a C1-C4 haloalkylene group, a divalent ether group derived from bisphenol A, a divalent ether group derived from bisphenol F, a divalent ether group derived from bisphenol S, or a divalent ether group derived from hexafluorobisphenol A, and G ４ Each of these independently represents a hydrogen atom, a substituted or unsubstituted hydrocarbon group with 1 to 30 carbon atoms, and a bond.

6. The photosensitive resin composition according to any one of claims 1 to 4, wherein polymer B comprises a polyimide represented by the following general formula (d). 【Transformation 5】 (In general formula (d), R ３ , R ４ Q ２ , G ４ This is equivalent to the above general formula (b), and there are multiple R ３ Multiple Rs exist ４ Multiple Qs exist. ２ Multiple Gs ４ The individuals may be the same or different. Y is selected from the groups represented by the following general formulas (d1), (d2), and (d3), and from the haloalkylene groups having 1 to 5 carbon atoms. Multiple Ys may be the same or different. 【Transformation 6】 (In general formula (d1), R ７ and R ８ Each of these independently represents a hydrogen atom, a C1-C3 alkyl group, or a C1-C3 alkoxy group, and there are multiple R groups. ７ Multiple Rs exist ８ The elements can be identical or different. * indicates a combination. In general formula (d2), R ９ and R １０ Each of these independently represents a hydrogen atom, a C1-C3 alkyl group, or a C1-C3 alkoxy group, and there are multiple R groups. ９ Multiple Rs exist １０ They may be the same or different. １１ R represents a hydrogen atom, an alkyl group having 1 to 3 carbon atoms, or an alkoxy group having 1 to 3 carbon atoms, and there are multiple R groups. １１ The elements can be identical or different. * indicates a combination. In the general formula (d3), Z represents an alkylene group having 1 to 5 carbon atoms, or a divalent aromatic group. * indicates a bonding position. Q ３ This represents a repeating unit expressed by the following general formula (d4). 【Transformation 7】 (In general formula (d4), R ５ , R ６ , and X is synonymous with the general formula (b1), G ４ (b) is equivalent to the above general formula (b), and Y is equivalent to the above general formula (d). n represents an integer between 20 and 200. * indicates a combination.

7. Furthermore, the photosensitive resin composition according to any one of claims 1 to 6, comprising a silane coupling agent.

8. A cured film comprising a cured product of the photosensitive resin composition according to any one of claims 1 to 7.

9. A semiconductor device comprising a resin film containing a cured product of the photosensitive resin composition according to any one of claims 1 to 7.

10. Interlayer insulating film and A resin film provided on the interlayer insulating film, comprising a cured product of the photosensitive resin composition according to any one of claims 1 to 7, The rewiring embedded in the aforementioned resin film, The semiconductor device according to claim 9, characterized by comprising:

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